quinidine   Click here for help

GtoPdb Ligand ID: 2342

Synonyms: Quinaglute® | Quinidex® | quinidine hydrochloride
Approved drug PDB Ligand Antimalarial Ligand
quinidine is an approved drug (FDA (1950))
Compound class: Natural product or derivative
Comment: Quinidine is a stereoisomer of quinine. It acts as a class I antiarrhythmic agent, blocking the fast inward sodium current (INa).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: quinidine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 45.59
Molecular weight 324.18
XLogP 2.6
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES C=CC1CN2CCC1CC2C(c1ccnc2c1cc(OC)cc2)O
Isomeric SMILES C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cc(OC)cc2)O
InChI InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19+,20-/m0/s1
InChI Key LOUPRKONTZGTKE-LHHVKLHASA-N
References
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Single-channel properties and pH sensitivity of two-pore domain K+ channels of the TALK family.
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10. Milligan CJ, Li M, Gazina EV, Heron SE, Nair U, Trager C, Reid CA, Venkat A, Younkin DP, Dlugos DJ et al.. (2014)
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TWIK-2, an inactivating 2P domain K+ channel.
J Biol Chem, 275 (37): 28722-30. [PMID:10887187]
12. Schönherr R, Gessner G, Löber K, Heinemann SH. (2002)
Functional distinction of human EAG1 and EAG2 potassium channels.
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13. Sheldon RS, Duff HJ, Thakore E, Hill RJ. (1994)
Class I antiarrhythmic drugs: allosteric inhibitors of [3H] batrachotoxinin binding to rat cardiac sodium channels.
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14. Snyders J, Knoth KM, Roberds SL, Tamkun MM. (1992)
Time-, voltage-, and state-dependent block by quinidine of a cloned human cardiac potassium channel.
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15. Sánchez-Carranza O, Torres-Rodríguez P, Darszon A, Treviño CL, López-González I. (2015)
Pharmacology of hSlo3 channels and their contribution in the capacitation-associated hyperpolarization of human sperm.
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16. Tang QY, Zhang Z, Xia XM, Lingle CJ. (2010)
Block of mouse Slo1 and Slo3 K+ channels by CTX, IbTX, TEA, 4-AP and quinidine.
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17. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K. (2007)
Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters.
Biochem Pharmacol, 74 (2): 359-71. [PMID:17509534]
18. Wang J. (2016)
The plasma membrane monoamine transporter (PMAT): Structure, function, and role in organic cation disposition.
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19. White NJ, Looareesuwan S, Warrell DA, Chongsuphajaisiddhi T, Bunnag D, Harinasuta T. (1981)
Quinidine in falciparum malaria.
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20. Wrighton DC, Muench SP, Lippiat JD. (2015)
Mechanism of inhibition of mouse Slo3 (KCa 5.1) potassium channels by quinine, quinidine and barium.
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21. Yamagishi T, Ishii K, Taira N. (1995)
Antiarrhythmic and bradycardic drugs inhibit currents of cloned K+ channels, KV1.2 and KV1.4.
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22. Yang B, Gribkoff VK, Pan J, Damagnez V, Dworetzky SI, Boissard CG, Bhattacharjee A, Yan Y, Sigworth FJ, Kaczmarek LK. (2006)
Pharmacological activation and inhibition of Slack (Slo2.2) channels.
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